In the ion-pair complex, bis[1-(naphthalen-1-ylmethyl)pyridinium] bis(2,2-dicyanoethene-1,1-dithiolate-κ2 S,S′)nickelate(II), C—H⋯N and C—H⋯Ni hydrogen bonds as well as π–π interactions between the ions result in the formation of a three-dimensional network.
Keywords: bis(2,2-bicyanoethene-1,1-dithiolato)nickel(II); pyridinium; hydrogen bonding; π–π interaction; crystal structure.
Abstract
A new ion-pair complex, (C16H14N)2[Ni(C4N2S2)2] or (1-NaMePy)2[Ni(imnt)2], where 1-NaMePy is 1-(4-naphthylmethylene)pyridinium and imnt is 2,2-dicyanoethene-1,1-dithiolate, was obtained by the direct reaction of NiCl2, K2imnt and (1-NaMePy)+Br− in H2O. The asymmetric unit contains a [1-NaMePy]+ cation and one half of an Ni(imnt)2 2− anion. The NiII ion lies on an inversion centre and adopts a square-planar configuration with Ni—S bond lengths of 2.200 (1) and 2.216 (1) Å. In the [1-NaMePy]+ cation, the naphthyl ringsystem and the pyridinium ring make a dihedral angle of 90.0 (2)°. In the crystal, C—H⋯N and C—H⋯Ni hydrogen bonds, as well as π–π interactions between the chelate ring and the pyridinium ring [centroid–centroid distance = 3.675 (2) Å] link the ions into a three-dimensional network.
Chemical context
Transition metal complexes with dithiolate ligands such as 2,2-dicyanoethene-1,1-dithiolate (imnt) or 1,2-dicyanoethene-1,2-dithiolate (mnt) are important molecular materials with interesting electrical conductivity, superconductivity, optical and magnetic properties (Liu et al., 1996 ▶; Robertson & Cronin, 2002 ▶; Ni et al., 2005 ▶; Ren et al., 2002 ▶; Xie et al., 2002 ▶; Duan et al. 2010 ▶). Recently, attempts have been made to extend the range of metal complexes containing the Ni(imnt)2
2− anion, and the topology and the size of some organic cations, such as substituted benzyl pyridinium derivatives, play an important role in tuning the stacks of anions and cations of molecular materials containing the Ni(imnt)2
2− anion (Liu et al., 2006 ▶; Feng et al., 2007 ▶). The title ion-pair complex, (1-NaMePy)2[Ni(imnt)2] has therefore been prepared and investigated. 
Structural commentary
The asymmetric unit of the title compound consists of one [1-NaMePy]+ cation and one-half of an Ni(imnt)2 2− anion located about an inversion center. The NiS4 core exhibits a square-planar configuration, with Ni—S bond lengths of 2.200 (1) and 2.216 (1) Å. The S1—Ni1—S2 bond angle within the four-membered ring (Ni1/S1/C1/S2) is 78.91 (3)°. The N1 and N2 atoms of the C N groups deviate from the Ni1/S1/C1/S2 plane by 0.078 (3) and 0.169 (3) Å, respectively. The [1-NaMePy]+ cation adopts a conformation in which both the naphthyl ring system and the pyridinium ring are twisted with respect to the N3/C11/C10 reference plane, making dihedral angles of 10.5 (2)° and 87.3 (3)°, respectively. The naphthyl ring system and the pyridinium ring make a dihedral angle of 90.0 (2)°.
Supramolecular features
There are three weak interactions between the Ni(imnt)2 2− anion and [1-NaMePy]+ cation. The first is a π–π contact between the chelate ring (which is defined by atoms Ni1, S1, S2, and C1) of the anion and the pyridinium ring of the cation (Fig. 2 ▶) with a distance of 3.675 (2) Å between the centroids. The second is a C—H⋯Ni hydrogen bond and the third is a C—H⋯N hydrogen bond (Table 1 ▶, Fig. 3 ▶). The combination of these weak interactions consolidates the title complex into a three-dimensional network structure (Fig. 3 ▶).
Figure 2.
The π–π contact between the chelate ring of the anion and the pyridinium ring of the cation (shown as a dashed line).
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C19—H19⋯N2i | 0.93 | 2.60 | 3.265 (5) | 129 |
| C20—H20⋯N1ii | 0.93 | 2.42 | 3.304 (5) | 160 |
| C15—H15B⋯Ni1iii | 0.97 | 3.07 | 3.508 (4) | 109 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Figure 3.
The packing of the title compound, viewed down the a axis, showing the network of molecules connected by C—H⋯N hydrogen bonds (dashed lines).
Database survey
Many ion-pair complexes containing Ni(imnt)2 2− anion have been reported, typical examples being [TBA]2[Ni(imnt)2] and [4NO2BzPy]2[Ni(imnt)2] [TBA is tetrabutylammonium; 4NO2BzPy is 1-(4-nitrobenzyl)pyridinium] (Liu et al., 2006 ▶), [4FBzPy]2[Ni(imnt)2] [4FBzPy is 1-(4-fluorobenzyl)pyridinium] (Zhou & Ni, 2007 ▶), [Bz2NH2Py]2[Ni(imnt)2] (Bz2NH2Py is 1-benzyl-2-aminopyridinium) (Hou et al., 2007 ▶), [BzDMAP]2[Ni(imnt)2] [BzDMAP is 1-benzyl-4-(dimethylamino)pyridinium] (Feng et al., 2007 ▶), [2-NaMePy]2[Ni(imnt)2] and [2-NaMe-4-MePy]2[Ni(imnt)2] [2-NaMePy is 1-(2-naphthylmethyl)pyridinium; 2-NaMe-4-MePy is 1-(2-naphthylmethyl)-4-methylpyridinium] (Huang et al., 2009 ▶), [Bz-4-MePy]2[Ni(imnt)2] and [Bz-4-MeQl]2[Ni(imnt)2] (Bz-4-MePy is 1-benzyl-4-methylpyridinium; Bz-4-MeQl is 1-benzyl-4-methylquinolinium) (Liu et al., 2013 ▶). For a description of C—H⋯N and C—H⋯Ni hydrogen bonds, see: Huang et al., (2009 ▶). For a description of π–π contacts between chelate and phenyl rings, see: Molčanov et al. (2013 ▶).
Synthesis and crystallization
The title ion-pair complex was prepared by the direct reaction of 1:2:2 mol equiv. of NiCl2·6H2O, K2imnt and 1-(4-naphthylmethylene)pyridinium bromide in water (Huang et al., 2009 ▶). The brown product obtained was purified through recrystallization from a mixed solvent of methanol and water (yield: 78%). Brown block-shaped single crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution at room temperature after about 4 weeks.
Refinement
All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, U iso(H) = 1.2U eq(C) for aromatic and d(C—H) = 0.97 Å, U iso(H) = 1.2U eq(C) for CH2 atoms. Crystal data, data collection and structure refinement details are summarized in Table 2 ▶.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | (C16H14N)2[Ni(C4N2S2)2] |
| M r | 779.63 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 291 |
| a, b, c (Å) | 11.876 (3), 9.025 (3), 17.465 (5) |
| β (°) | 91.808 (4) |
| V (Å3) | 1871.0 (9) |
| Z | 2 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.78 |
| Crystal size (mm) | 0.36 × 0.30 × 0.21 |
| Data collection | |
| Diffractometer | Bruker SMART CCD area detector |
| Absorption correction | Multi-scan (SADABS; Bruker, 2000 ▶) |
| T min, T max | 0.762, 0.843 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 9345, 3283, 2228 |
| R int | 0.031 |
| (sin θ/λ)max (Å−1) | 0.595 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.040, 0.102, 1.04 |
| No. of reflections | 3283 |
| No. of parameters | 232 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.21, −0.15 |
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814017012/kp2472sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017012/kp2472Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814017012/kp2472Isup3.cml
CCDC reference: 1015644
Additional supporting information: crystallographic information; 3D view; checkCIF report
Figure 1.
The molecular structure of (I), with the atom labelling and 30% probability displacement ellipsoids for non-H atoms The other half of the anion is generated by the inversion-symmetry operation −x, y + 
, −z + .
Acknowledgments
The authors thank the Doctor’s Foundation of Huanggong Normal University (10CD001) and the Educational Commission of Hubei Province of China (Q20112902) for financial support.
supplementary crystallographic information
Crystal data
| (C16H14N)2[Ni(C4N2S2)2] | F(000) = 804 |
| Mr = 779.63 | Dx = 1.384 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1994 reflections |
| a = 11.876 (3) Å | θ = 2.5–22.7° |
| b = 9.025 (3) Å | µ = 0.78 mm−1 |
| c = 17.465 (5) Å | T = 291 K |
| β = 91.808 (4)° | Block, brown |
| V = 1871.0 (9) Å3 | 0.36 × 0.30 × 0.21 mm |
| Z = 2 |
Data collection
| Bruker SMART CCD area detector diffractometer | 3283 independent reflections |
| Radiation source: fine-focus sealed tube | 2228 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.031 |
| φ and ω scans | θmax = 25.0°, θmin = 2.3° |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −13→14 |
| Tmin = 0.762, Tmax = 0.843 | k = −9→10 |
| 9345 measured reflections | l = −20→20 |
Refinement
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.102 | H-atom parameters constrained |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.046P)2 + 0.1262P] where P = (Fo2 + 2Fc2)/3 |
| 3283 reflections | (Δ/σ)max < 0.001 |
| 232 parameters | Δρmax = 0.21 e Å−3 |
| 0 restraints | Δρmin = −0.15 e Å−3 |
Special details
| Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
| Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Ni1 | 0.0000 | 0.0000 | 0.0000 | 0.06043 (19) | |
| S1 | 0.03025 (7) | 0.02841 (8) | 0.12405 (4) | 0.0697 (2) | |
| S2 | 0.08762 (7) | 0.21679 (9) | 0.00355 (4) | 0.0709 (2) | |
| N1 | 0.2232 (3) | 0.5408 (4) | 0.11604 (17) | 0.1156 (12) | |
| N2 | 0.1247 (3) | 0.2483 (3) | 0.29836 (16) | 0.0963 (9) | |
| N3 | 0.2381 (2) | 0.7148 (3) | 0.42980 (16) | 0.0805 (7) | |
| C1 | 0.0909 (2) | 0.1950 (3) | 0.10140 (14) | 0.0616 (7) | |
| C2 | 0.1329 (2) | 0.2957 (3) | 0.15460 (14) | 0.0628 (7) | |
| C3 | 0.1819 (3) | 0.4313 (4) | 0.13254 (16) | 0.0792 (9) | |
| C4 | 0.1274 (3) | 0.2685 (3) | 0.23417 (17) | 0.0704 (8) | |
| C5 | 0.4644 (3) | 0.7646 (4) | 0.4864 (2) | 0.1009 (11) | |
| H5 | 0.4408 | 0.7981 | 0.4382 | 0.121* | |
| C6 | 0.5731 (3) | 0.8033 (5) | 0.5164 (3) | 0.1080 (13) | |
| H6 | 0.6212 | 0.8604 | 0.4875 | 0.130* | |
| C7 | 0.6062 (3) | 0.7565 (4) | 0.5872 (2) | 0.1045 (12) | |
| H7 | 0.6768 | 0.7843 | 0.6069 | 0.125* | |
| C8 | 0.5373 (3) | 0.6678 (4) | 0.6314 (2) | 0.0817 (9) | |
| C9 | 0.5710 (3) | 0.6177 (4) | 0.7054 (2) | 0.0983 (11) | |
| H9 | 0.6410 | 0.6467 | 0.7255 | 0.118* | |
| C10 | 0.5068 (4) | 0.5308 (5) | 0.7473 (3) | 0.1114 (13) | |
| H10 | 0.5314 | 0.4992 | 0.7956 | 0.134* | |
| C11 | 0.4017 (4) | 0.4881 (5) | 0.7169 (3) | 0.1169 (14) | |
| H11 | 0.3563 | 0.4266 | 0.7455 | 0.140* | |
| C12 | 0.3642 (3) | 0.5342 (4) | 0.6470 (2) | 0.0957 (11) | |
| H12 | 0.2933 | 0.5047 | 0.6286 | 0.115* | |
| C13 | 0.4307 (3) | 0.6261 (3) | 0.6015 (2) | 0.0769 (9) | |
| C14 | 0.3947 (3) | 0.6786 (4) | 0.5280 (2) | 0.0812 (9) | |
| C15 | 0.2770 (3) | 0.6348 (4) | 0.4999 (2) | 0.1096 (13) | |
| H15A | 0.2759 | 0.5292 | 0.4895 | 0.131* | |
| H15B | 0.2246 | 0.6539 | 0.5402 | 0.131* | |
| C16 | 0.2514 (4) | 0.6590 (5) | 0.3620 (3) | 0.1198 (14) | |
| H16 | 0.2866 | 0.5676 | 0.3573 | 0.144* | |
| C17 | 0.2150 (5) | 0.7315 (7) | 0.2989 (3) | 0.1362 (19) | |
| H17 | 0.2264 | 0.6917 | 0.2506 | 0.163* | |
| C18 | 0.1615 (4) | 0.8632 (6) | 0.3060 (3) | 0.1177 (15) | |
| H18 | 0.1346 | 0.9136 | 0.2627 | 0.141* | |
| C19 | 0.1477 (3) | 0.9203 (4) | 0.3761 (3) | 0.1004 (11) | |
| H19 | 0.1118 | 1.0109 | 0.3821 | 0.120* | |
| C20 | 0.1868 (3) | 0.8436 (4) | 0.43750 (19) | 0.0822 (9) | |
| H20 | 0.1775 | 0.8821 | 0.4863 | 0.099* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.0607 (3) | 0.0696 (4) | 0.0503 (3) | 0.0003 (3) | −0.0087 (2) | −0.0033 (2) |
| S1 | 0.0793 (5) | 0.0764 (5) | 0.0527 (4) | −0.0091 (4) | −0.0100 (4) | 0.0017 (4) |
| S2 | 0.0824 (5) | 0.0771 (5) | 0.0528 (4) | −0.0074 (4) | −0.0057 (4) | −0.0001 (4) |
| N1 | 0.173 (3) | 0.094 (2) | 0.080 (2) | −0.040 (2) | −0.010 (2) | 0.0011 (17) |
| N2 | 0.130 (3) | 0.097 (2) | 0.0603 (16) | 0.0021 (18) | −0.0146 (16) | −0.0046 (15) |
| N3 | 0.0765 (18) | 0.083 (2) | 0.0818 (19) | −0.0104 (15) | −0.0064 (15) | 0.0020 (16) |
| C1 | 0.0571 (16) | 0.0696 (18) | 0.0577 (15) | 0.0041 (14) | −0.0062 (13) | −0.0005 (14) |
| C2 | 0.0666 (18) | 0.0695 (19) | 0.0517 (16) | −0.0009 (15) | −0.0079 (13) | −0.0009 (14) |
| C3 | 0.100 (3) | 0.081 (2) | 0.0552 (18) | −0.008 (2) | −0.0128 (17) | −0.0031 (17) |
| C4 | 0.076 (2) | 0.072 (2) | 0.0625 (19) | 0.0008 (16) | −0.0157 (15) | −0.0052 (16) |
| C5 | 0.079 (2) | 0.106 (3) | 0.118 (3) | −0.009 (2) | −0.004 (2) | 0.026 (2) |
| C6 | 0.068 (2) | 0.118 (3) | 0.139 (4) | −0.026 (2) | 0.012 (2) | 0.022 (3) |
| C7 | 0.079 (3) | 0.111 (3) | 0.122 (3) | −0.014 (2) | −0.011 (2) | 0.005 (3) |
| C8 | 0.065 (2) | 0.071 (2) | 0.109 (3) | −0.0020 (17) | 0.005 (2) | −0.004 (2) |
| C9 | 0.084 (3) | 0.102 (3) | 0.108 (3) | 0.007 (2) | −0.015 (2) | 0.006 (2) |
| C10 | 0.103 (3) | 0.127 (3) | 0.104 (3) | 0.017 (3) | −0.005 (3) | 0.019 (3) |
| C11 | 0.097 (3) | 0.120 (3) | 0.133 (4) | 0.010 (3) | 0.003 (3) | 0.047 (3) |
| C12 | 0.070 (2) | 0.100 (3) | 0.117 (3) | 0.000 (2) | −0.002 (2) | 0.028 (2) |
| C13 | 0.064 (2) | 0.0643 (19) | 0.103 (2) | 0.0054 (16) | 0.0043 (19) | 0.0066 (18) |
| C14 | 0.063 (2) | 0.077 (2) | 0.103 (2) | −0.0091 (17) | −0.0005 (18) | 0.0121 (19) |
| C15 | 0.086 (3) | 0.119 (3) | 0.122 (3) | −0.025 (2) | −0.024 (2) | 0.046 (3) |
| C16 | 0.143 (4) | 0.103 (3) | 0.114 (3) | 0.002 (3) | 0.019 (3) | −0.020 (3) |
| C17 | 0.184 (5) | 0.153 (5) | 0.073 (3) | −0.048 (4) | 0.010 (3) | −0.032 (3) |
| C18 | 0.117 (4) | 0.140 (4) | 0.094 (3) | −0.035 (3) | −0.030 (3) | 0.034 (3) |
| C19 | 0.095 (3) | 0.095 (3) | 0.111 (3) | −0.003 (2) | −0.007 (2) | 0.012 (3) |
| C20 | 0.088 (2) | 0.086 (2) | 0.072 (2) | −0.013 (2) | −0.0014 (18) | −0.0120 (19) |
Geometric parameters (Å, º)
| Ni1—S1i | 2.2000 (9) | C8—C9 | 1.415 (5) |
| Ni1—S1 | 2.2000 (9) | C9—C10 | 1.329 (5) |
| Ni1—S2i | 2.2160 (9) | C9—H9 | 0.9300 |
| Ni1—S2 | 2.2160 (9) | C10—C11 | 1.395 (6) |
| S1—C1 | 1.718 (3) | C10—H10 | 0.9300 |
| S2—C1 | 1.719 (3) | C11—C12 | 1.353 (5) |
| N1—C3 | 1.144 (4) | C11—H11 | 0.9300 |
| N2—C4 | 1.137 (3) | C12—C13 | 1.409 (4) |
| N3—C16 | 1.300 (5) | C12—H12 | 0.9300 |
| N3—C20 | 1.321 (4) | C13—C14 | 1.420 (4) |
| N3—C15 | 1.482 (4) | C14—C15 | 1.519 (4) |
| C1—C2 | 1.382 (4) | C15—H15A | 0.9700 |
| C2—C3 | 1.414 (4) | C15—H15B | 0.9700 |
| C2—C4 | 1.415 (4) | C16—C17 | 1.342 (6) |
| C5—C14 | 1.361 (4) | C16—H16 | 0.9300 |
| C5—C6 | 1.421 (5) | C17—C18 | 1.355 (6) |
| C5—H5 | 0.9300 | C17—H17 | 0.9300 |
| C6—C7 | 1.353 (5) | C18—C19 | 1.344 (5) |
| C6—H6 | 0.9300 | C18—H18 | 0.9300 |
| C7—C8 | 1.395 (5) | C19—C20 | 1.346 (5) |
| C7—H7 | 0.9300 | C19—H19 | 0.9300 |
| C8—C13 | 1.406 (4) | C20—H20 | 0.9300 |
| S1i—Ni1—S1 | 180.00 (4) | C9—C10—H10 | 120.8 |
| S1i—Ni1—S2i | 78.91 (3) | C11—C10—H10 | 120.8 |
| S1—Ni1—S2i | 101.09 (3) | C12—C11—C10 | 121.6 (4) |
| S1i—Ni1—S2 | 101.09 (3) | C12—C11—H11 | 119.2 |
| S1—Ni1—S2 | 78.91 (3) | C10—C11—H11 | 119.2 |
| S2i—Ni1—S2 | 180.00 (4) | C11—C12—C13 | 121.1 (4) |
| C1—S1—Ni1 | 86.09 (9) | C11—C12—H12 | 119.5 |
| C1—S2—Ni1 | 85.56 (10) | C13—C12—H12 | 119.5 |
| C16—N3—C20 | 120.2 (3) | C8—C13—C12 | 117.5 (3) |
| C16—N3—C15 | 121.3 (4) | C8—C13—C14 | 119.2 (3) |
| C20—N3—C15 | 118.5 (3) | C12—C13—C14 | 123.2 (3) |
| C2—C1—S1 | 124.5 (2) | C5—C14—C13 | 120.1 (3) |
| C2—C1—S2 | 126.1 (2) | C5—C14—C15 | 122.9 (3) |
| S1—C1—S2 | 109.42 (15) | C13—C14—C15 | 117.0 (3) |
| C1—C2—C3 | 121.9 (2) | N3—C15—C14 | 113.6 (3) |
| C1—C2—C4 | 121.3 (3) | N3—C15—H15A | 108.8 |
| C3—C2—C4 | 116.8 (3) | C14—C15—H15A | 108.8 |
| N1—C3—C2 | 178.5 (4) | N3—C15—H15B | 108.8 |
| N2—C4—C2 | 178.7 (4) | C14—C15—H15B | 108.8 |
| C14—C5—C6 | 120.3 (4) | H15A—C15—H15B | 107.7 |
| C14—C5—H5 | 119.9 | N3—C16—C17 | 120.9 (4) |
| C6—C5—H5 | 119.9 | N3—C16—H16 | 119.5 |
| C7—C6—C5 | 119.6 (3) | C17—C16—H16 | 119.5 |
| C7—C6—H6 | 120.2 | C16—C17—C18 | 119.4 (4) |
| C5—C6—H6 | 120.2 | C16—C17—H17 | 120.3 |
| C6—C7—C8 | 121.7 (4) | C18—C17—H17 | 120.3 |
| C6—C7—H7 | 119.1 | C19—C18—C17 | 119.4 (4) |
| C8—C7—H7 | 119.1 | C19—C18—H18 | 120.3 |
| C7—C8—C13 | 119.0 (3) | C17—C18—H18 | 120.3 |
| C7—C8—C9 | 122.3 (3) | C18—C19—C20 | 118.7 (4) |
| C13—C8—C9 | 118.6 (3) | C18—C19—H19 | 120.7 |
| C10—C9—C8 | 122.7 (4) | C20—C19—H19 | 120.7 |
| C10—C9—H9 | 118.6 | N3—C20—C19 | 121.3 (3) |
| C8—C9—H9 | 118.6 | N3—C20—H20 | 119.3 |
| C9—C10—C11 | 118.4 (4) | C19—C20—H20 | 119.3 |
Symmetry code: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C19—H19···N2ii | 0.93 | 2.60 | 3.265 (5) | 129 |
| C20—H20···N1iii | 0.93 | 2.42 | 3.304 (5) | 160 |
| C15—H15B···Ni1iv | 0.97 | 3.07 | 3.508 (4) | 109 |
Symmetry codes: (ii) x, y+1, z; (iii) x, −y+3/2, z+1/2; (iv) −x, y+1/2, −z+1/2.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814017012/kp2472sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017012/kp2472Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814017012/kp2472Isup3.cml
CCDC reference: 1015644
Additional supporting information: crystallographic information; 3D view; checkCIF report